72 Questions Startup Founders Should Ask Business Mentors

Every startup founder should carefully select industry leaders equipped to guide them with knowledge, resources, and connections to build better businesses. This mentor network can be an essential ingredient to side-stepping mishaps, boosting confidence, and ultimately navigating the bumpy road that is entrepreneurship.

Mentor relationships must be beneficial to both parties, so leverage your time with advisors effectively by asking meaningful questions to support your objectives – and theirs!  Get the most out of your mentor meetings (and, frankly, not waste their time). Here are 72 questions to consider asking when you have an expert’s attention:

  1. How do I communicate value to stakeholders, such as investors, clients, users. etc?
  2. What is the most crucial leadership skill that you’ve learned and how do you suggest I apply it to my own business?
  3. What are the keys to a great business pitch?
  4. Failure is part of the process with entrepreneurship. How did you learn to overcome setbacks?
  5. I’m considering a pivot or new product for my business. What do you think are the pros and cons of doing this?
  6. If you had the opportunity, what would you have done differently with your business/product/service/career?
  7. How did you stage growth for your business? Can you share stories of how you scaled your company?
  8. How do you know if you are ready to launch a new product or service line?
  9. How did you learn to share your message with others? Do you have any tips about how I can improve?
  10. What advice do you have to make my business more operationally efficient?
  11. How do you suggest that I measure progress?
  12. Where do you see my strengths and what should I focus on improving?
  13. Do I have any blind spots in my business? Am I missing anything?
  14. When you first started working, did you foresee that this is where you would be?
  15. Tell me about a time when you had a difficult time running your business. How did you manage it?
  16. From email to meetings, how do you organize your day?
  17. What habits help you be effective with your productivity?
  18. What do you consider to be your greatest strength? How did you become competent in this area?
  19. What advice do you have for delegating responsibilities to my team and/or hired help?
  20. What tools do you suggest (for HR, accounting, marketing automation, etc.)?
  21. What were some of your previous weaknesses? How did you overcome them?
  22. What is something positive that you see in me that I need to focus on?
  23. What advice do you have for maintaining life-balance?
  24. What three aspects of business building do you think are most important for early-stage founders?
  25. Tell me about a setback you experienced, and how you recovered?
  26. What are your tips for managing and overcoming burnout?
  27. What advice do you have to making meetings more effective?
  28. Can you give me examples of how you handled difficult situations?
  29. How can I communicate my ideas or business more clearly?
  30. What traits do see are commonly held by great entrepreneurs?
  31. Risk is such a big part of business. How do you approach taking risks?
  32. What skills do you think are necessary for me to grow as a leader?
  33. Who do you suggest that I can connect with to help me with this specific aspect of my business?
  34. I feel overwhelmed. How do I prioritize what I need to do to move ahead?
  35. How do I develop trust within business relationships, including with employees, vendors, contractors, or others?
  36. What advice can you offer for me progress my business over the next 30/90/180 days?
  37. What skills do I need to get ahead?
  38. How can I become more assertive to getting what I want?
  39. How can I improve at being a better manager?
  40. How do I measure differentiation among my competitors? What advice do you have for standing out in my market?
  41. Who or what experience influenced you the most in your career?
  42. Business can challenge your beliefs and assumptions about your product. What do you suggest for measuring, acting upon, challenging, or keeping to convictions associated to business?
  43. How does equity work?
  44. What do investors look for?
  45. How do I communicate the pressures of what I do to my family, friends, and personal relationships?
  46. How have you managed personal relationships when in the trenches of building your businesses?
  47. When do you know if your business is ready for changes?
  48. How do you find your inspiration to keep going?
  49. What books/newsletters/blogs/podcasts/resources do I suggest and why?
  50. If you had the opportunity, what would you have done differently with your business/product/service/career?
  51. How do you approach unknown challenges?
  52. What is necessary for a strategic plan?
  53. How do you keep your feelings from clouding your decision-making?
  54. What are some other opportunities I’m missing to monetize or improve the financial returns of my business?
  55. How do you bring courage and conviction to risky situations?
  56. How do you create a mission for your business?
  57. What are your tips to effectively network?
  58. How do you cultivate effective business relationships?
  59. How do you define success in business/as a leader/human?
  60. How do you measure ROI in xyz area?
  61. Based on your understanding of my business, what values should I be marketing?
  62. What are you learning right now?
  63. What do you see as my greatest challenge and how do you suggest that I overcome it?
  64. What do you hope to teach me through mentorship?
  65. What do you hope to gain from mentoring me?
  66. What can I do to make this process more rewarding for both of us?
  67. Who do you know that might be of help to my current business situation/problem?
  68. What financial numbers should I be focused on right now?
  69. What makes my company attractive to outside stakeholders?
  70. How do I convert users/clients to my business? Can you give me examples of how have you done this?
  71. Which software/product/service do you use to help you with xyz area of my business?
  72. How do you do a self-assessment of your progress?

Build your startup with a business mentor

Remember: Your mentor can guide you to answers, but shouldn’t tell you what to do. If you are the owner, founder, or executive of a company, decisions should fall to you. No one should know your business better than you do. Mentors can absolutely help you succeed, but your mentors, no matter how mighty they are, aren’t responsible for your achievement. You are.

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